HCID 86725405, compound → HCID 82646980, compound

HRID 1503866Notes

Reaction equation

HRID 1503866 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:5][C:4]=1[N+:22]([O-])=O>CO.[Ni]>[NH2:22][C:4]1[CH:5]=[C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 1

HCID 86725405HCID 86725405, compound

Product 1

HCID 82646980HCID 82646980, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of the product of Example 46A (260 mg, 0.77 mmol) and Raney-Ni (50 mg) in methanol (10 mL) was stirred under hydrogen at ambient temperature for 15 hours. The solution was filtered through diatomaceous earth and the filtrate was concentrated. The residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with a gradient of 3/1 to 2/1 petroleum/ethyl acetate to give the title compound.

Workup

  1. filtrationThe solution was filtered through diatomaceous earth
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by flash chromatography on silica gel (200-300 mesh)
  4. washeluting with a gradient of 3/1 to 2/1 petroleum/ethyl acetate

Sources & evidence

ORD record
ord-48371ff5175c49248f3818e7a956bcce
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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